The five times Cas and Dean kissed
by Sugar.SomeSpice
Summary: And the one time Dean remembered. Six chapters of Destiel goodness. Enjoy!
1. The First Time

**I do not own any characters from Supernatural. Although, I wish I had Charlie. Meow.  
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**Part one. The angel who realized the beauties of daydreaming.**

Sam and Dean were fighting, over some trivial thing. It was not of importance to Cas, he had no time for meaningless arguments about shampoo.

"I'm not a horse, Dean." Sam yelled, "You don't have to buy me horse shampoo."

"You're lucky I bought you shit!" Dean returned, sending a mischievous look to Cas.

The angel fidgeted in his seat, he wasn't sure why Dean looked at him like that. It was a normal thing for them, to stare too long, to stand too close. (He'd heard a song about this) Castiel always thought that was a normal, everyday thing.

Apparently, to the women of _The View _it was not. These wise women said that these were all signs of infatuation.

Cas paid no mind to it, these women were probably insane, but as time passed he realized that they were right. Except the infatuation was only one sided. According to "Dear Abby" this was called unrequited love. Dean didn't love Cas, but Cas loved him. It was a simple notion, easy to understand, although very painful.

"Dear Abby" suggested that anyone who was in an unrequited love situation get away from the object of their affection soon or else they would only fall deeper and deeper in love.

Cas didn't believe that was true but as he watched Dean's lips rise into a small grin he knew he was falling. Cas wanted to lean in to taste Dean's lips, but all he could do was imagine it. Cas frowned, perhaps he should get away from Dean. Although, he was too far in to ever leave.

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Every time you leave a review an angel gets his wings.


	2. The Second Time

******I do not own any characters from Supernatural. Although, if I did I wouldn't have killed off the only female demon I ever liked!**

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**Part two. The Angel, The Bitch, and the Hunter that needs to keep his mouth shut.**

"Dean! Come on, Dean! Wake up, please wake up." Sam pleaded at the stoic body that lay on the ground, "What did you do to him?" Sam asked viciously, tears of anger welling in his eyes, his hand inching towards the rifle that lay beside him.

"Moi?" The witch daintily laid a hand over her collar bone, feigning innocence, "I did nothing. Really, Sammy-"

"Don't call me that." Sam said through clenched teeth.

"-I am shocked. I am the good witch, remember?" Sam let out a long breath, it was true. Sam had asked Simone for help to look for another witch. (Simone was an exceptional tracker). He didn't tell Dean because Dean wasn't one to trust witches, or any supernatural creature, or any _one_ for that matter. So, obviously, when Dean realized that Simone was not a _human_ tracker he wasn't exactly happy, at all. He called Simone a few names that weren't very nice.

"You asked for my help, Sam." Simone broke Sam's train of thought, "I gave you my help, for free! Then this ape goes on a rampage and calls me a **_bitch_**_**.**_ I will not tolerate that."

"But he's not dead, right?" Sam asked scrambling up to his feet.

"No." Simone pursed her lips, "I am not even going to tell you I would kill him because I would never!" She turned to leave but Sam ran after her.

"Simone, please, what do I do?" She could see the pain that was etched out across his face and as much as she ached for Sam, she felt no remorse for cursing Dean.

She shrugged, "He'll sleep it off... I think."

"_You think." She turned to leave, "Wait_, don't go." But Simone didn't even glance his way, she just continued down the road. Sam ran a hand through his hair and took a long, shaky breath.

_'Okay. I can do this."_He looked down at Dean who seemed to give a deep snort in response, _'I can totally do this.'_

He couldn't.

"Cas? Um... A little help here?' Sam raised his hands helplessly after a long beat of silence, "I could really use it."

The sound of wings clapping together came from the back of Sam, "I was on my way." Castiel's deep voice explained. Sam turned to see Castiel kneeling on the floor beside Dean, "I am sorry if I did not respond as soon as you called, I was preoccupied.

Sam scoffed, not fully believing him, "What, were you stuck in angel traffic?"

Cas tilted his head, "Sam, if you are under the impression that angels drive vehicles, you are incorrect. I thought you of all people would know." Sam smirked and decided to let it go, "Although, I have been taking lessons."

Sam furrowed his brow, "Lessons? Who's teaching you?" Cas looked down at Dean, "Really? That's actually _sweet_."

"It is not meant to be. Dean is merely being a good friend."

Sam knelt down beside Dean and sent a smile to Cas. He wasn't too sure if Cas saw, he was staring intently at Dean. Sam knew that he was trying to figure out what he could do to help but there was something behind the angels blue eyes that worried Sam. His eyes were like a calm storm that burned with silent desire. Sam hoped that the look in his eyes stayed hidden in them, he didn't want there to be secrets that would hurt his brother or the angel he learned to call his friend.

"Cas?"

"Yes, Sam?"

Sam sighed, "You know if you ever need to talk, I'm here." Cas looked confused but he seemed to appreciate the sentiment. "You know, if Sleeping Beauty here doesn't wake up soon we're going to have to put him in the Impala."

"Sleeping Beauty?" Cas questioned Sam's choice of words, obviously confused.

"Yeah, you know." Cas did not, "The princess that was cursed by that witch and woke up when her prince kissed her."

Cas nodded in response, taking Sam's silly joke too seriously. And in that moment when Castiel's lips touched Deans, Sam was sure he felt his stomach explode.

"What are you doing?" Sam practically screeched.

But Cas could not reply because as soon as he opened his mouth Dean shot up from the ground, breathing frantically.

"What the hell happened?" Dean twisted from side to side, "Cas? Sam? Where's the witch?" Dean seemed to remember then and he sent a cold glare at Sam. "You know what, I don't want to know. I'm tired and I just want a beer. Let's go back to the motel."

"Dean…" Sam began.

"Keys, Sammy." Dean held his hand out and Sam reluctantly gave them to him.

As Dean walked to the car he smiled at Cas and asked him if he would be joining them but Castiel mumbled something about other priorities and the disappointment in Deans voice did not go unnoticed by Sam.

The angel made his way towards his pale, traumatized, friend, "Sam?"

Sam gulped, "Erm, yeah?"

"Perhaps it would be best if you kept the events that transpired today to yourself." Cas turned to look at the other Winchester who was sitting the driver seat, squinting his eyes at the two men, "And away from your brother."

"Believe me Cas, you don't have to tell me twice."

Cas gave him a weak, tired smile and vanished. Sam desperately wished that he would get the image of his brother and his brother's angel kissing out of his mind, but he knew that this was just the start of something really, really bad.

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**Every time you leave a review an angel gets his wings.**


	3. The Third Time

**Part three. The girl who needed to go to prom and the angel that keeps getting boners.**

Sam should have seen it coming.

Dean wasn't exactly Dean; he hadn't been Dean all morning. But he really paid no attention to it. So maybe it was weird when "Dean" came into the motel with a large smile on his face and a plastic container with a slice of cake in it instead of pie, or that he picked up and edition of people instead of busty Asian beauties. It was weird, but Sam didn't pay attention to it and he really should have.

As Dean enjoyed his cake, a blissful smile forming on his lips as he chewed, Sam read up on potential cases. His eyes ached and his body hurt, he swore that last night would be the last time he stayed up watching reruns of _Oprah_.

"Sammy?" Dean called from the other side of the room.

"You know, you shouldn't talk with your mouth open. It isn't very charming." Sam smiled at the snort Dean gave in response.

"I'm not trying to charm anyone, you'd know if I was trying to charm anyone." Dean took another bite of cake as if it were an act of defiance, "Anyway, I saw a strip club down the street and I was wondering if you wouldn't mind if I went. And, you know, left you with all of this..." Dean motioned to the files that sat a Sam's feet, "'...stuff."

"Are you asking me?" Dean was silent, "You never ask. But I guess you can go, I don't mind."

A goofy smile replaced the tentative the one that was on Dean's lips, "Cool." Dean cleared his throat, "I can help you before I leave. It's way too early anyway."

As Dean made his way towards Sam the younger Winchester let out an incredulous laugh, "Who are you and what have you done with my brother?"

Dean froze for a split second, Sam was sure he saw it. It was quick, and if you blinked you would have missed it but he still froze.

"Very funny, Sammy, don't be paranoid, I can be a good brother every once and a while." He grabbed a handful of files and flipped through them.

"You can be a great brother." The corners of Dean's lips twitched upward, "I just- you know what, forget it." Sam realized that good things rarely come for him and if he could keep Dean in this mood forever, he would.

Dean smiled, opened his mouth and prepared to speak, but was graciously interrupted by their angels gravely voice.

"I sensed that one of you was calling for me, very loudly if I may add."

Dean's smile faltered and his cheeks gracefully changed from a healthy pink to an embarrassing red.

"Hi Cas!" Dean exclaimed, throwing his right arm up to wave enthusiastically.

Cas arched one eyebrow and turned to Sam, who was just as confused at his brothers behavior, "You are not Dean."

He accused.

Dean, or not Dean so it seemed, stamped his foot on the floor like a child throwing a tantrum, "Aw, man. How'd you know?"

Cas stepped forward, his body language was threatening and his hands were balled up at his sides, "Who are you?" He demanded, his welcoming, kind features hardening with anger at the prospect of someone hurting his friend. (Or not friend)

It was pretty embarrassing, experiencing sexual attraction, it wasn't something Cas understood. And he didn't like it either. It was like having warmth spread all over your body, warmth that was pleasurable but also annoying, like an inch you can't scratch or a taste that won't leave your tongue. Cas couldn't get the feel of Dean's lips off of his own. He didn't "French" Dean (Cas likes to watch TV, he knows things like this) but it was a sweet kiss, one that he would have like to have if he was a young human boy experiencing it for the first time.

'Dean' sighed, Castiel's inner monologue leaving and his pants suddenly tight at the recollection of Dean's lips, "I'm just hitching a ride. I promise I won't hurt him. Please, I really just need to make it to my prom."

"Prom?" Cas questioned, his voice coming out higher that usual.

Sam seemed to register the situation finally and spoke up, "Wait a minute." The two men in front of him turned around "Are you some teenager with raging hormones that took my brother as a host so you could go to your prom?"

Dean jutted his hip to the right and rested his hands at the corner of his hips, the stance of a beach blonde beauty that didn't get the correct order of coffee, "Um, yeah"

"Do I want to know?" Sam asked, his eyelids heavy from the lack of sleep.

"Look, I missed out on prom in the 90's, stupid Stacy Bride ran me over and hid me in a ditch. Then the crazy bitch had the decency to take my shoes, like, honestly." Sam raised his eyebrows, it seemed like she was more upset over the shoes than her actual hit and run. "I just want to go to prom; I want to experience everything I missed out on."

"You're dead." Cas explained, his morose voice not helping the sensitivity of the situation, "You don't have the chance to experience anymore."

Dean's eyes began to water and his bottom lip began to tremble, Sam's eyes widened with realization and suddenly a loud shriek reverberated throughout the motel room. Dean fell to the floor, tears streaming down his face and snot bubbles coming out of his nose.

"No." Sam halfheartedly soothed the ghost in Dean's body, "No, no, shhh. Don't cry, oh don't cry. Oh, no, no." Sam looked over at Cas, whose eyes were wide with onder. He'd never seen Dean cry before, well, at least not so enthusiastically. Sam motioned to the angel, his head jerking in an unnatural manner.

Cas sighed as he walked over to then, his hands replacing Sam's as they gently patted his back, "What is your name?"

'Dean' sniffed, "Michelle." It was a broken noise, not at all fake, but genuinely saddened at the realization of her errors, "I just wanted to go to prom."

"I understand." Cas didn't really understand. Prom was still very confusing. Was it similar to that of human matrimony or was it a type of rite of passage that humans took in order to pass into adulthood? I didn't matter though; all Cas wanted was to have Dean back, _his_ Dean. "But I," Cas looked over at Sam, "_we_ would really appreciate it if you found another body to haunt."

Sam was going to suggest that Michelle try to let go and move on and away from life here on earth but he couldn't because Michelle jumped forward and attacked Cas's mouth. Sam watched in horror, his face crumbling in mortification. _Oh, __**God**__! Was that tongue?_

Michelle let go, "I'm sorry. I am SO sorry. That wasn't me, that wasn't me! You have to believe me, it was-" Dean's body crumbled forward and Cas caught him before he hit the ground.

Cas could not understand, even with the taste of Dean's tears and the fact that it wasn't actually Dean, it was him. He felt it, he felt Dean in the kiss. He felt his anger and his beauty, he felt _Dean._

Dean shook his head in Cas's arms and lifted himself up to his feet. "Woah!" He exclaimed, "I'm glad that crazy bitch is gone. No offence or anything but I could not understand anything that was going on."

Sam, who was still reeling from the shock, cleared his throat, "So, you, you remember anything?"

"No. I could talk to her, she told me why she needed my body and what kinds of things I liked but I only told her cuz I felt bad." Dean explained, clearly lying. Sam knew that the girl had an affect on Dean, he probably actually connected with her and wanted to help her but Dean kept being Dean. Stubborn bastard. "But I could think, I just couldn't see anything that was going on. I called for you." Dean pointed at Cas.

"What?" Sam and Cas asked at the same time.

"Yeah. I was thinking of way to get the chick out of him and I thought of you, so I called and you came." Cas blinked and remembered hearing Dean's frantic voice but he didn't understand how he was able to hear him, "But I don't remember anything. Why did something happen?" It grew quiet, "I feel great though. Really, really-"And that's when he preceded to throw up on Sammy's shoes.

Cas would still kiss him even if he was throwing up cake on Sam, that's when Cas realized what love truly meant.


	4. The Fourth Time

**Part four. The angel who dressed as a devil and the hunter that danced with him.**

"I'd like to know what you mean by _masquerade ball_." Dean asked, his mouth falling into a disgusted frown as he spoke the last two works.

Sam's face morphed into his signature 'bitch face' and Dean glared at him, "What I mean," Sam threw a bowtie at Dean's face, "is masquerade ball. Dean this is a rouge cupid we've got on our hands, there have been five deaths so far." Dean rolled his eyes, "And this ball is going to be this bastard's final showdown, he wants to go with a bang."

Dean opened his mouth, "Don't start with me, Dean." Sam stopped him before he could speak. It wasn't like Sam to be a, well, dick, but he couldn't get over the event that took place weeks ago. The kiss, the one that Dean did not remember and Castiel could not get over.

Sam couldn't tell why he was more upset because Dean was so blind or because Castiel was so hopelessly in love. The younger Winchester had complete and utter faith in his brother's angel, even when he was being an ass, but right now Dean took up most of his thoughts. Sam tried to be a shoulder to cry on; the person who could be honest with Cas when he needed someone the most, but it was hard.

For one, Sam couldn't hear half the fantasies that Cas had about his brother. In the beginning it was understandable but after Cas mentioned something about Dean in fishnets and high heels Sam couldn't take it anymore. They decided that feelings were okay to talk about; sex fetishes were a total no-no.

"Fine!" Dean threw his hands up in defense, "Sorry, I just don't like feathers and glittery shit."

Sam breathed a laugh, "It's not feathers and glittery shit." Sam walked in front of Dean and passed him a beer, "I think that you're just freaked out because it's a chick thing."

Dean chuckled and shook his head, "Sammy, you know me all too well." He crumbled the bowtie into a ball and tossed it into Sam's face, "But you are bat shit crazy if you think I'm going to wear a bow tie."

"You did once." Sam returned, remembering the events that took place with Bela years ago, "You didn't look _that_ bad."

"I looked fucking sexy, but ties bring out my cheekbones." He slammed the motel bathroom door leaving Sam behind to ponder his thoughts. He wondered how he was going to tell Dean that it was a costume masquerade, and he was going to be a peacock.

II.

"Why do I have to be a peacock?!" Dean cried out. Sam appraised his brother's look and stifled a laugh. Dean shot him a cold, hard glare but Sam just covered the laugh with a cough, "I don't care if it's Halloween or not, this is stupid. It's not funny, Sam. I've got feathers coming out of my ass."

"Classy." Sam handed their keys to the valet and walked up the concrete stairs.

"Why do you have to be a knight?" Dean whined, "I wanna be a knight."

"Sorry, you're a little to short for this costume." Dean huffed in annoyance, "Besides I think you look cute. You didn't have to put on the face makeup."

Dean scoffed, honestly insulted, "What kind of person puts on the feathers but not the make up? I had to coordinate." Sam pondered this and watched as Dean made a beeline to the bar.

"Try not to smudge your lipstick." He saw as Dean struggled to not raise his hand up to tell him exactly how he felt. If they were ever going to catch this son of a bitch cupid then Dean needed to act the part.

Sam heard a light moan come from behind him, "Aren't these strawberries to die for!" He turned, not exactly knowing what to expect but the tall, skinny, devilishly handsome individual seemed to charm all of the people who circled him, men and women. And that's when Sam realized who he was, he was their rogue cupid.

They made eye contact and Sam stood straighter in response, the cupid seemed to think Sam was flustered but he was actually just preparing himself for the attack. The cupid licked him lips and blew a kiss to Sam earning a cold glare from the rest of cupids followers.

"Sammy!" He pushed passed his eager group, "I was expecting you." Sam stayed quiet and looked around for Dean, "Your brother is fine, do not worry, he's off having fun." He motioned to Dean dancing with a man in devil mask that covered almost all of his face, "Not my doing of course. You're brother just seems to have a particular taste in his lovers and he _loves_ to dance with the devil, doesn't he?"

"We're here to stop you." The cupid laughed, his fiery green eyes glowing with amusement. Sam pursed his lips together in an attempt to calm himself; Castiel had warned him about the power of cupids. They fed off of love and this particular cupid only wanted lust.

The last few cases the Winchesters encountered all had people who died because of… strenuous sexual activity. They pretty much had sex until they died one couple of a heart attack, another pair that starved themselves for days because they locked themselves in a room. Sam knew how tough it was going to be to kill this asshole, but he was hoping on a miracle. He felt the angel sword that was hidden in his "armor" and gripped it tight, glad that Castiel trusted him with it.

"But maybe," Sam began, "You could, show me around first?" Sam asked, fluttering his eyelashes flirtatiously and acting his part out perfectly. He already discussed the plan with Castiel and told Dean another story. The cupid smirked and placed his hand at the small of Sam's back. Sam looked down at the hand in horror but did not flinch away; this is what he called "taking one for the team."

Dean on the other hand was having the time of his life; he was whisked away into the arms of a masked man. It was weird but it was also kinda hot. Like in those movies when some tall, dark, and handsome fellow walked in and the entire room froze, except you couldn't see this guys face he just had one of those demeanors. But Dean's not gay! He must stress _how he is __**not**__gay_.

"Do you normally pick up peacocks while they're ordering drinks?" Dean asked as the devil pulled his body closer and tightened his grasp around Dean's hip.

"No, but I liked your feathers." The voice explained before twirling Dean in a small circle. Dean would never admit it, it was surprising that he was even admitting it to himself, but he liked being led. The devil knew how to move him and made him feel protected. Dean's head began to hurt; those words should not be used in the same sentence. "Besides, I feel like you need a good dance."

"No. Not a good dance but maybe something else." Dean laughed, his voice dripping with suggestion.

The stranger lifted his mask and leaned over to Dean, his lips brushing past his ear, his warm breath sending shiver of anticipation down Dean's back, "Well, if you stay until the end of this event I'll let you take this mask off, amongst other things."

"We just met." Dean breathed out, his voice sounding shakier than he intended.

The stranger laughed, "I'm sure you wouldn't mind."

Dean furrowed his brow and put his hands on his partner's lean chest, hands pushing against him and away from Dean. It was the fact that they were in the same room as a cupid, this is why Dean wanted him so badly, it was why all he wanted to do was throw himself onto the masked man and ravish him on the dance floor.

He is not gay.

Not that being gay was a bad thing but he was not _gay._

Dean gulped, he felt as if the whole room could hear him and then he noticed something, something he hadn't noticed before; the familiar neck of the stranger in front of him. He reached out to touch it, to caress the skin that he knew he had seen before.

"I know you." Dean whispered, as he gently wrapped his hand around his stranger's neck. In any other situation someone would have thought they were about to fight but the action left the masked man vulnerable to Dean and Dean had him in his hand. It was a touch of pure affection

His hand made his way to cup his jaw and he lifted the mask up ever so slightly, just so see the lips of the stranger. He looked only for a second and not any longer before the pink lips of the stranger collided against his own, leaving Dean with the taste of hunger and passion. It was tantalizing and mesmerizing, it left him wanting more. But how could he obtain anymore? He felt full and complete, for the first time in a long time he felt wanted.

It ended sooner than he expected, the bitter aftertaste of ecstasy was left on his tongue and the only way to extinguish it was to have his lips again, "I've never kissed a devil before." Dean whimpered under the strangers touch.

"I've never kissed a peacock."

Dean laughed and looked down at the man in front of him with amazement, "You're really something, whoever you are."

"ARRRGGHHHH!" A loud scream erupted throughout the hall and echoed down the stairs that Sam had just followed the cupid up. A white light emitted quickly before vanishing, reminding Dean of the angels he'd seen die in front of him. Although, this light was not as bright, it burned Dean's enough to make him look away.

Sam came running right after the light, looking like a knight running from a burning castle after he'd just vanquished the fearful dragon. Dean half expected Sam to make some cheesy about freedom from the top of the staircase but he just ran down in front of Dean and pulled him towards the entrance.

Dean was about to protest but he saw that his devil was missing and the ache he felt coerce throughout his body was enough to silence him. He was really looking forward to taking off the strangers mask, and the other things he promised.

Dean was intrigued by the stranger but he felt a slight guilt pulling at his heart. He thought of Cas and how he would react and Dean felt he had cheated. He told his head to keep quiet but his heart burned and he felt like he was going to throw up, he hadn't even realized they were in the car until Sam had asked him if he was going to put his seatbelt on.

"Wuh?" Dean garbled and he blinked tiredly at Sam.

Sam quirked his eyebrow and shook his head, "Um, nothing. Nevermind." Sam stared at him until he started the car and pulled out of the long driveway.

"So," Dean started, his usual 'what-the-hell' persona coming to life, "mind telling me what the hell happened back there?"

Sam shuddered at the thought and looked at his brother, pleading, "Dean, you really, _really, _don't want to know."

Dean nodded and took a good, hard look at his brother, "Sammy?"

"Yeah?

Dean struggled with his words, "You've got a- You've got some chocolate sauce on your cheek."

Sam wiped his face quickly and avoided eye contact with him, "You smeared your make up, and it looks, horrible. What'd you do, make out with someone?' Sam chuckled, but Dean froze.

"What 'bout some tunes?" The rest of the car ride was quiet and tense as the two Winchesters sat with make up and chocolate sauce on their face, evidence of their Halloween fun.

It wasn't until Cas woke Sam up in the middle of the night with blue lipstick covering his mouth that Sam realized that he was right about his previous accusation.


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